(1R,5R,6R)-5-Ethylsulfanylcarbonyl-4-methyl-6-(2-methyl-propenyl)-2-oxo-cyclohex-3-enecarboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,5R,6R)-5-Ethylsulfanylcarbonyl-4-methyl-6-(2-methyl-propenyl)-2-oxo-cyclohex-3-enecarboxylic acid methyl ester
• 英文别名: methyl (1R,5R,6R)-5-ethylsulfanylcarbonyl-4-methyl-6-(2-methylprop-1-enyl)-2-oxocyclohex-3-ene-1-carboxylate
• 化学式: C₁₆H₂₂O₄S
• 分子量: 310.414
• InChiKey: RXSOIUNPJLXEKC-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  85.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6,6-trimethyl-6h-pyran-3-carbothioic acid S-ethyl ester 、 Arsonium, (4-methoxy-2,4-dioxobutyl)triphenyl-, bromide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到(1R,5R,6R)-5-Ethylsulfanylcarbonyl-4-methyl-6-(2-methyl-propenyl)-2-oxo-cyclohex-3-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Novel Michael-Wittig reactions of methyl 3-oxo-4-(triphenylarsoranylidene)butanoate and substituted 2H-pyran-5-carboxylates; The synthesis of highly functionalised 2-cyclohexenonedicarboxylates

  摘要：

  Novel Michael-Wittig condensations of methyl 3-oxo-4-(triphenylarsoranylidene)-butanoate 6 and substituted 2,2-dimethyl-2H-pyran-5-carboxylates 5a to 5e gave substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8a to 8e in a mixture of three keto diastereomers and two enol diastereomers. Apart from substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8f to 8g, less hindered substituted 2-methyl-2H-pyran-5-carboxylates 5f and 5g gave the substituted tetrahydrobenzofurans 9f and 9g. 4-Halomethyl-6-oxo-4-cyclohexene 1,1-dicarboxylates 8 were mostly in the enol diastereomeric form. A plausible mechanism is given for the unique formation for these products. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01126-x

文献信息

• Novel Michael-Wittig reactions of methyl 3-oxo-4-(triphenylarsoranylidene)butanoate and substituted 2H-pyran-5-carboxylates; The synthesis of highly functionalised 2-cyclohexenonedicarboxylates
  作者：Cornelis M. Moorhoff

  DOI：10.1016/s0040-4020(96)01126-x

  日期：1997.2

  Novel Michael-Wittig condensations of methyl 3-oxo-4-(triphenylarsoranylidene)-butanoate 6 and substituted 2,2-dimethyl-2H-pyran-5-carboxylates 5a to 5e gave substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8a to 8e in a mixture of three keto diastereomers and two enol diastereomers. Apart from substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8f to 8g, less hindered substituted 2-methyl-2H-pyran-5-carboxylates 5f and 5g gave the substituted tetrahydrobenzofurans 9f and 9g. 4-Halomethyl-6-oxo-4-cyclohexene 1,1-dicarboxylates 8 were mostly in the enol diastereomeric form. A plausible mechanism is given for the unique formation for these products. (C) 1997, Elsevier Science Ltd.

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